JP6957807B2 - 右旋性オキシラセタムの２型結晶、調製方法および用途 - Google Patents
右旋性オキシラセタムの２型結晶、調製方法および用途 Download PDFInfo
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- JP6957807B2 JP6957807B2 JP2019519399A JP2019519399A JP6957807B2 JP 6957807 B2 JP6957807 B2 JP 6957807B2 JP 2019519399 A JP2019519399 A JP 2019519399A JP 2019519399 A JP2019519399 A JP 2019519399A JP 6957807 B2 JP6957807 B2 JP 6957807B2
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- oxyracetam
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- crystal
- Prior art date
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 72
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
- 239000012046 mixed solvent Substances 0.000 claims description 37
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 36
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- 239000000706 filtrate Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 24
- 238000001914 filtration Methods 0.000 claims description 20
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 18
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- SUHOOTKUPISOBE-UHFFFAOYSA-N O-phosphoethanolamine Chemical compound NCCOP(O)(O)=O SUHOOTKUPISOBE-UHFFFAOYSA-N 0.000 description 2
- 206010039897 Sedation Diseases 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000008499 blood brain barrier function Effects 0.000 description 2
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- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
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- 230000037361 pathway Effects 0.000 description 2
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 description 2
- 229950004354 phosphorylcholine Drugs 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
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- 241000473391 Archosargus rhomboidalis Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
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- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 201000007186 focal epilepsy Diseases 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
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- 239000007779 soft material Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610985131 | 2016-10-24 | ||
| CN201610985131.9 | 2016-10-24 | ||
| PCT/CN2017/092220 WO2018076783A1 (zh) | 2016-10-24 | 2017-07-07 | 右旋奥拉西坦晶型ii及其制备方法和用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2019536751A JP2019536751A (ja) | 2019-12-19 |
| JP6957807B2 true JP6957807B2 (ja) | 2021-11-02 |
Family
ID=62012293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019519399A Active JP6957807B2 (ja) | 2016-10-24 | 2017-07-07 | 右旋性オキシラセタムの２型結晶、調製方法および用途 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10793521B2 (zh) |
| EP (1) | EP3530271A4 (zh) |
| JP (1) | JP6957807B2 (zh) |
| KR (1) | KR20190051059A (zh) |
| CN (1) | CN107973739B (zh) |
| WO (1) | WO2018076783A1 (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018076784A1 (zh) | 2016-10-24 | 2018-05-03 | 重庆润泽医药有限公司 | （r）-4-羟基-2-氧代-1-吡咯烷乙酰胺晶型及其制备方法和用途 |
| KR20190053253A (ko) | 2016-10-24 | 2019-05-17 | 충칭 룬즈 파마슈티컬 컴퍼니 리미티드. | 덱스트랄 옥시라세탐의 새로운 결정형, 이의 제조 방법 및 이의 용도 |
| JP6957807B2 (ja) | 2016-10-24 | 2021-11-02 | チョンキン ランゼ ファーマスーティカル カンパニー リミテッド | 右旋性オキシラセタムの２型結晶、調製方法および用途 |
| CN108299267A (zh) | 2017-01-12 | 2018-07-20 | 重庆润泽医药有限公司 | (r)-4-羟基-2-氧-1-吡咯烷乙酰胺的晶型及其制备方法和用途 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1075280B (it) | 1977-02-11 | 1985-04-22 | Isf Spa | Procedimento per la preparazione di derivati pirrolidinici |
| IT1075564B (it) | 1977-02-11 | 1985-04-22 | Isf Spa | Procedimento per la preparazione di derivati pirrolidinici |
| KR100679633B1 (ko) | 2004-07-27 | 2007-02-07 | 한국화학연구원 | 광학 활성을 갖는 옥시라세탐의 제조 방법 |
| ES2587978T3 (es) * | 2010-05-21 | 2016-10-28 | Chongqing Runze Pharmaceutical Co., Ltd. | Forma cristalina de (s)-4-hidroxi-2-oxo-1-pirrolidina acetamida, método de preparación y uso de la misma |
| CN102442936A (zh) * | 2010-10-09 | 2012-05-09 | 重庆润泽医疗器械有限公司 | 一种(s)-4-羟基-2氧代-1-吡咯烷乙酰胺的纯化方法 |
| CN102603607B (zh) | 2011-01-21 | 2014-06-11 | 温州智创科技有限公司 | （r）-奥拉西坦的制备方法 |
| CN102249977B (zh) * | 2011-08-11 | 2013-06-12 | 重庆润泽医药有限公司 | 4-羟基-2-氧代-1-吡咯烷乙酰胺外消旋体晶型ⅰ及其制备方法 |
| CN102558013B (zh) * | 2011-08-11 | 2013-12-18 | 重庆润泽医药有限公司 | (s)- 4-羟基-2-氧代-1-吡咯烷乙酰胺晶型ⅱ及其制备方法 |
| CN102600130A (zh) * | 2012-03-26 | 2012-07-25 | 北京阜康仁生物制药科技有限公司 | 奥拉西坦及其光学异构体的新临床用途 |
| CN103554000B (zh) * | 2013-11-06 | 2015-03-11 | 重庆润泽医药有限公司 | (s)-奥拉西坦晶型iii及其制备方法和用途 |
| CN103553998B (zh) | 2013-11-06 | 2015-11-25 | 温州智创科技有限公司 | (s)-奥拉西坦晶型iii的制备方法 |
| CN105330582B (zh) * | 2014-08-07 | 2018-08-07 | 重庆润泽医药有限公司 | (r)-4-羟基-2-氧代-1-吡咯烷乙酰胺的制备方法 |
| CN105820101B (zh) | 2015-01-04 | 2018-12-18 | 哈尔滨三联药业股份有限公司 | 一种旋光纯1-(氨基甲酰基)甲基-4-羟基-2-吡咯烷酮的制备方法 |
| US20180147183A1 (en) * | 2015-05-18 | 2018-05-31 | Chongqing Runze Pharmaceutical Co., Ltd. | Use of r-oxiracetam in pharmaceutical field |
| KR20190053253A (ko) | 2016-10-24 | 2019-05-17 | 충칭 룬즈 파마슈티컬 컴퍼니 리미티드. | 덱스트랄 옥시라세탐의 새로운 결정형, 이의 제조 방법 및 이의 용도 |
| JP6957807B2 (ja) | 2016-10-24 | 2021-11-02 | チョンキン ランゼ ファーマスーティカル カンパニー リミテッド | 右旋性オキシラセタムの２型結晶、調製方法および用途 |
| WO2018076784A1 (zh) | 2016-10-24 | 2018-05-03 | 重庆润泽医药有限公司 | （r）-4-羟基-2-氧代-1-吡咯烷乙酰胺晶型及其制备方法和用途 |
| CN108299267A (zh) | 2017-01-12 | 2018-07-20 | 重庆润泽医药有限公司 | (r)-4-羟基-2-氧-1-吡咯烷乙酰胺的晶型及其制备方法和用途 |
-
2017
- 2017-07-07 JP JP2019519399A patent/JP6957807B2/ja active Active
- 2017-07-07 CN CN201710551920.6A patent/CN107973739B/zh active Active
- 2017-07-07 US US16/344,338 patent/US10793521B2/en active Active
- 2017-07-07 EP EP17863355.8A patent/EP3530271A4/en not_active Withdrawn
- 2017-07-07 KR KR1020197011746A patent/KR20190051059A/ko not_active Application Discontinuation
- 2017-07-07 WO PCT/CN2017/092220 patent/WO2018076783A1/zh active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| KR20190051059A (ko) | 2019-05-14 |
| CN107973739A (zh) | 2018-05-01 |
| CN107973739B (zh) | 2020-03-20 |
| EP3530271A4 (en) | 2020-03-25 |
| EP3530271A1 (en) | 2019-08-28 |
| US10793521B2 (en) | 2020-10-06 |
| US20190256464A1 (en) | 2019-08-22 |
| WO2018076783A1 (zh) | 2018-05-03 |
| JP2019536751A (ja) | 2019-12-19 |
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